You'd known the Wheeler's for years, now - having grown up in the same social circles as Theodore 'Ted' Wheeler and his relatives, like the rest of your family - though, you lost touch after you grew up.
It wasn't 'til a few years after you finished college - realising how much you actually missed Hawkins (despite it pretty much being a dump) - that you managed to find them again (not that it was that hard, considering how small the town is), and the new additions - Nancy (6 when you first met her, now going into her junior year of high school), Mike (2 when you first met him, now going into his last year of middle school), and Holly (who wasn't in the picture when you came back, but was now gonna be in your 1st grade class, just like her older brother and sister, before her).
Not to mention Karen (Ted's wife, though it wasn't exactly the happiest of marriages, which isn't necessarily a secret to most people, but no one's ever really broached the subject with much seriousness), who you remember being in the same year as Karen Childress; cheerleader, minor theatre kid, and secret nerd. Gorgeous, amazing, caring, Karen.
You'd gotten to know her more, over the years, often giving her space to just be herself, instead of 'Mom' or 'Ted's wife', when you have had the chance to talk properly; falling in love with her more and more, every time you saw her. Which (between that, and unintentionally reconnecting with Ted) ended up with you having a bit of a regular figure in their kids lives, helping out whenever and wherever you could, with whatever any of them would approach you for.
Despite this (though, you're not sure how exactly, considering you adored the three of them immensely), you managed to keep your personal connection with the family out of teaching them, as to not give them any kind of (what could be perceived as) unfair advantages (not that it was too difficult, since it was only two separate years); until now.
Since you'd last had a Wheeler in your classroom, your feelings for Karen had grown and grown and grown, occasionally causing you to cross certain lines amongst the family's dynamic (considering how Ted does pretty much fuck-all around the house), 'To help her out' you mentally excused, at first (not that Karen ever opposed otherwise, even if you had crossed those boundaries more than what's comfortable for her), but you're not sure what would be a plausible explanation, now - On the first day of Holly's kindergarten year.
Everything had gone smoothly so far, 'til you got pulled aside by your class assistant, Ms B., who informed you that Holly and her mom were in the hall. After excusing yourself to go and help with that, you were greeted with the fairly familiar sight of Karen, flustered, trying to negotiate with Holly, to see what solutions could work, when problems weren't easily identifiable; the girl's backpack having been discarded on a bench next to them.
"Hey, what's going on out here?" You asked softly, moving to kneel down in front of Holly, who was half hiding behind Karen's leg.
"Holly wanted to bring her stuffy with her, but we already talked about not being able to do that, cause there's so many toys here, it might get lost." Karen replied, while threading her fingers through one of the younger blonde's pigtails.
"And... I'm guessing she smuggled him in anyway?" You questioned, filling in the blanks. Not that Karen had to say anything, the answer was obvious; 'Yes'.
"Well, y'know something, Holly? I have a really big, polar bear stuffy on the windowsill, next to my desk, and he watches over the kids in my class, as a favour, to all their plushies, to make sure they don't get scared, while they're not with them." You explained, having grown used to giving this kind of talk.
"Polar bear?" Holly repeated timidly, coming out from behind Karen's leg slightly.
"Uh huh- Wanna go check him out, while I talk with your mom?" You offered.
"Yeah!" She said, speeding off towards your classroom.
"Thank you." Karen spoke up, with a tired sigh, after a moment.